Chicago’s most famous nickname is the Windy City, and though the name’s origins have more to do with corrupt local politicians, the weather always delivers. The city is known for its sweltering hot summers, unpredictable and inconsistent temperatures in the spring and fall, and unbearably frigid winters. Don’t go in unprepared.
Out-of-towners might expect some snow flurries and chilly winds in November and December, but locals know the truth. The truly freezing Chicago winter season doesn’t set in until January and lasts through March, when temps are known to dip below zero, freeze the pipes and slick the roads. Chicago isn’t the only American city that gets bitterly cold, but it is one of the most brutal, and battle-ready. Even in single digits and buried under several feet of snow, the city chugs on. Schools are unlikely to close and residents continue about their business.
Dress for the Weather
This might seem obvious, but it’s also easy to go wrong. February is probably the least fashionable time of year for Chicago because everyone is so bundled up that they’re reduced to a pile of heavy fabric and a set of eyes squinted against the snow. A simple jacket is not going to cut it. Think: thick, insulated coat (maybe two), fleece-lined snow boots, hat, gloves and scarf. Stock up along Michigan Avenue while doing your holiday shopping. The North Face has everything you need at their large store in the John Hancock Center. Just across the street is Columbia Sportswear if you’re looking for something a bit more specialized, and Macy’s at Water Tower Place is always a reliable option for the basics.
Destinations Unlocked:Let our travel expert Stefano help you find your perfect Culture trip
Looking for an expert's perspective?Uncover my top 3 recommended places from each continent on the map.
1. GuatemalaAn express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.
2. BelizeA quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
3. MexicoAn exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
1. EcuadorA remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.
2. PeruAn alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
1. ItalyThe ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.
2. ScotlandEmbark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
3. PortugalA wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
1. South KoreaDiscover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.
2. ThailandFrom Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
3. Sri LankaA fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
1. MoroccoAn epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!
2. EgyptFrom Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
Learn the lay of the land
If you have a flexible schedule, steer yourself away from Lake Michigan as much as possible. The closer you are to the water, the more likely it is you will feel the impact of lake-effect wind and temperatures. (It’s always colder by the lake.) Sometimes it’s unavoidable, but when possible spend your free time exploring west side neighborhoods like Wicker Park, Logan Square, Greektown or Pilsen. Take a ride on the Brown Line and get cozy in Lincoln Square. If you’re someone who likes exercising outdoors all year round, consider jogging or biking the popular new 606 trail rather than the beaten lake path.
Drink something hot
Never underestimate the power of a hot drink. If you have any sort of walking commute to work or school, you’re going to want something steamy for the trip. Grab a cup of coffee from a place like Pickwick Coffee Roasting Co., whose quaint and cutesy Loop location (tucked in an alleyway off Jackson Avenue) is made for those in a rush. Or sit and stay awhile at one of these ten different citywide locations to indulge in a decadent hot chocolate. They’re sure to warm you up from the inside out.
Eat something hot
The two go hand-in-hand. Winter is the best time for steamy soups, thick stews and warm comfort meals. Try out one of Wow Bao’s six Chicagoland locations on your lunch break for noodles, rice and hot Asian buns. Latinicity in the Loop brings the spirit of Latin America and the heat of its cuisine to Chicago in their open-concept food court layout. And for dinner and drinks visit The Globe Pub in west Lakeview. You’ll get a plateful of hearty English fare like fish and chips, bangers and mash and shepherd’s pie as well as all the international beer you can drink.
Know your escape route
Sometimes it’s just not enough to be dressed properly with a warm drink in hand; the Chicago cold finds its way in. When this happens, have a few hideaways in mind to escape to when you just can’t bear to walk another block. Go beyond the crowded coffee chains and drugstores and find places that will be worth your warm-up time. Downtown, the Chicago Cultural Center is the perfect spot to enjoy in some free (heated) culture. You can duck in for one of their music, dance or theatre performances, hear a lecture, catch a screening or just wander the rotating art exhibits until you can feel your feet again. Similarly, the Harold Washington Library Center on State Street is a massive literary haven waiting for you with a warm chair. Spend a few hours here getting work done or simply exploring the building. Stroll through the top floor Winter Garden to feel the sun without the cold or check out one of their monthly art tours always on display.
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meet our Local Insider
HOW LONG HAVE YOU BEEN A GUIDE?
WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
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Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.